


dean's foray into sex toys

by jhoom



Category: Supernatural
Genre: Anal Fingering, Deansturbation, Dildos, M/M, Masturbation, Sex Toys, dean accidentally realizing he's into cas, you know the usual
Language: English
Status: Completed
Published: 2016-06-29
Updated: 2016-06-29
Packaged: 2018-07-19 02:26:03
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,850
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7340875
Author URL: https://archiveofourown.org/users/jhoom/pseuds/jhoom
Summary: <blockquote class="userstuff">
              <p>Dean's always wanted to try something, but he's never had the guts to do it.  But the bunker gives him the perfect opportunity, and fuck yeah he's going to take it.</p>
            </blockquote>





	dean's foray into sex toys

**Author's Note:**

> short little ficlet inspired by [this nsfw drawing](http://gachichubbs.tumblr.com/post/86549730666/green-sparkly-dildo-is-his-fav-the-last-nsfw-comm) (aka me being unable to focus on the things i'm supposed to be writing when a beauty like this comes across my dash lol)
> 
> come visit me on tumblr [@jhoomwrites](http://jhoomwrites.tumblr.com/) :)

There are things Dean’s always wanted to... try.  Sexy... things.  But he’s always been afraid about doing it.  The excuses were easy to come by.  First there was never ever any privacy when he’d been hunting with his dad.  None whatsoever.  When he was on his own, hunting by himself was just so damn _stressful_  he didn’t have the time or energy.  Then he was back with Sammy and he’d lamented the missed opportunity.

Not that it would’ve mattered.  Because there are other excuses, too.  How would he... go about it?  There are stores, that he knows, but he’s mortified by the _idea_  of walking into one and browsing and buying or (god forbid) needing to _ask for help_.  And they move around all the friggin time, right?  So it’s not like he can order one online.  So for years, Dean deals with a curiosity, a _desire_  he can’t indulge because he can’t.  Obviously.  Oh well.

It takes a few weeks of actually settling in to the bunker when he realizes the excuses are gone.

He has privacy.  His own fucking room for the first time in his adult life.

He has time.  Sure, they hunt.  A lot.  And there are world threatening disasters.  But in between, there is some legitimate down time.  

They have a P.O. box with an honest to god address on it.  They order shit online all the time.  And not just weird spellbooks or ingredients.  Boxes and boxes of DVDs or comics or who the fuck knows what else Sam buys himself.  They make regular mail runs.  No one would question Dean receiving a package or even bother asking what was inside.

The only real excuse left is that he’s fucking terrified.  Thinking is one thing, doing is a whole other one.  So while he plays with the idea in his head, visits a few sites and does research, he doesn’t actually _act_ on the impulse for a few more months.  

It takes Charlie casually mentioning how much _she_  enjoys certain sex toys (totally grossing out Sam, who’s not really a prude but can’t get over thinking of Charlie as a sister and therefore it just weirds him out).  Then, once he’s safe in his room with the gentle glow of the laptop screen encouraging him, he makes a few purchases.

He checks the tracking number obsessively for days, watches it make its progress across the country until it arrives in their mailbox.  Dean’s excuse that he’s on a beer run isn’t _terrible_ , but honestly he doesn’t really check to see if Sam bought it before he’s out the door.  The package is heavy - literally and metaphorically - in his hands as he takes it from the post office.  The website promised discretion and he’s glad to see that’s the case.  

The difficult part turns out to be playing it cool when he gets back to the bunker.  Sam shows little to no interest in the box tucked safely under Dean’s arm (at least not once he learns it’s not for him).  But it would be fishy if he just disappeared as soon as he got home.  So he quickly drops it off in his room before returning to help with dinner.

Hours pass until he finds a reasonable time to excuse himself to bed.  

Dean takes meticulous care in opening the box and taking out the contents one by one.  He’s new to this, so he didn’t go overboard.  Plus a huge box would’ve alerted Sam that something was up.  So there are only three things in the box.  Lube.  Butt plug.  Dildo.  

He takes a deep breath and considers his options.  

He’s done _things_  with guys before, but there’s a huge difference between blowjobs traded in the bathroom of some seedy bar or hasty handjobs in the back of a car.  This is... this is a big step, even if it’s one he’s taking by himself.  And he’s nervous, okay?  This is a big fucking deal because this is something he’s ~~wanted~~ been curious about for as long as he can remember, and now he’s finally going to indulge himself.

Five slow, deep breaths, then he opens up the dildo, grabs the lube, and heads to his bed.

In an ideal world, he’d have a partner to help him through this.  But this is far from an ideal world, at least when it comes to Dean Winchester, so his only guide is the extensive amount of porn he’s watched and reading he’s done over the past few days.  He’s already half hard just _thinking_  about it.

Meticulously he undresses himself and spreads out a towel on the bed.  He positions himself in the center, pointedly ignoring his cock for now so he can focus on opening the lube.  Slowly, he teases his hole until he relaxes.  The feeling is... different.  Not as exciting as he’d hoped, but definitely intriguing.  

It takes him an agonizing amount of time to work himself open.  He’s not used to it, first of all, and his unease makes his movements stiff and choppy.  Eventually Dean manages to get out of his own head, to focus solely on his breathing and the feelings.  It’s enough to get his dick curving against his belly and three fingers working steadily inside himself.  

He focuses a little as he tries to find his prostate.  He’s always ~~fantasized~~ wondered what it might be like, if it’s everything it’s cracked up to be.  With as much precision as he can muster, he continues to work his fingers in and out as he slowly searches for-

“Oh _fuck,”_ he gasps and arches his back up off the bedspread.  That was... _intense_.  He brushes the same spot again and again, just to be sure, and _yeah_  that’s definitely it.  That’s... that’s really fucking nice.  Fuck, why hasn’t he ever done this before?

Once it’s to the point where he can’t _stand_  it anymore, when he knows he’ll come if he doesn’t stop, he pulls his fingers out.  The tight band of muscle clenches around nothing and Dean winces at a loss for something he didn’t even know he wanted until a few moments ago.  

Grabbing the lube, he hastily applies a generous amount to the dildo.  He might feel empty right now, but the girth of the dildo is far more intimidating than his three fingers.  And sure, it’s great right now but he’s worried this’ll turn painful real quick if he’s not careful.

Even going slowly, just the head of the dildo breaching his hole, Dean feels the burn of being stretched.  He gasps and writhes as he continues to push inside, doing his best to force himself to relax.  He slips back into breathing deeply, shutting out as much as he can until he’s worked the dildo all the way in.  

He calms down and looks to see it buried in his ass, the green edges just visible in his hand.  And he can’t help it, but a giggle bubbles up inside of him.  He’s doing it, he’s _finally_  fucking doing it _god yes_.  

So he gets to it, moving it in and out, trying different angles and speeds until his dick isn’t just hard but aching and leaking all over the place.  

Now, the thing is, _this_  has always been the fantasy.  The sex toys and experimenting with them by himself.  Fuck, he’s gotten himself off on that countless times.  But now the reality of it is able to push him closer and closer to orgasm, but not quite enough to get there.  Giving in to the sensations is _amazing._ Watching as he fucks himself senseless, hand moving on his cock to the same rhythm as the dildo - goddamn, it’s _glorious_.

Yet it’s just... not _enough_.  Dean’s dangling on the precipice of coming all over himself, but he’s missing that little _push_  to get him there.  As his body frantically rides out wave after wave of pleasure, climbs higher and higher to ecstasy, his near blissed out mind searches for images that can get him there.

But- dammit...  God damn, _none_  of his usual spank bank material is cutting it.  Thinking about blowjobs or fucking someone just don’t _work_  with what he’s doing.  So he gives his subconscious free reign to come up with more suitable imagery.  Someone strong, with broad shoulders, who could manhandle him onto his back.  Would have worked him open with sure hands and then bent him in half to fuck him.  

Yeah that’s-  That’s better.  Much better.

He picks up the speed, throws his head back and imagines rough stubble nibbling along his collarbone, up his neck, his jaw, just the corners of his lips, not giving in to his whining, his begging for a proper kiss.  And the gentle way he’d nuzzle by Dean’s ear and whisper _filthy_  filthy words of praise would be _perfectly_  at odds with the rough way he’d thrust into him.

“Fuck... harder, baby... so good,” Dean moans.  He’s lost in the picture he’s created, doesn’t hear himself and couldn’t care less.

Euphoria erupts as he starts to hit his prostate in earnest, each thrust causing his cock to throb in his hand and leak more precome.  “Oh _god_ , right there...”  

His imagined lover, so attentive, would shift all his focus on doing it again and again, would _adore_  the noises he’s wringing out of Dean.  The image of the man on top of him, pounding him into his mattress, solidifies a little more in the form of a gravel rough voice whispering,  _“Come for me, Dean.”_

“Oh fuck.. fuck... Cas... don’t stop, Cas... Cas!”

Come streaks clear up to his chest as Dean falls into sheer joyful pleasure.  His hand continues to work the dildo into him until his overstimulated body clenches uncomfortably and he’s forced to withdraw it.  His body tingles all over and it’s just so fucking _good_.

And to the casual observer, it would look like Dean is taking it all in stride.  That sure, his first time fucking himself open he’d somehow started thinking about his best friend, but hey, that’s not a big deal.  Which is the only way to explain the calm expression and fucked out looseness in his limbs.

Until the peace is broken when he slams both hands over his face and screams “FUCK!” as loudly as he can.   ~~Actually, he should now be worried that Sam will come investigate.  Thankfully he remembered to lock his door.~~

Then it’s painfully obvious that Dean is _not handling this well_  and drowning in questions like  _what the hell did he just do_  and _what the actual fuck._

The panic subsides quickly, however, as he starts to re-imagine his earlier fantasy, this time from the very beginning putting Cas in the place of the nameless, featureless stranger.  Cas coming into his room and striping him naked, opening him up under his watchful eye while he strokes himself leisurely with his other hand.  

Then, quite frankly, Dean’s hard again and starting on round two.  

He can finish freaking out later, he’s got a bit more _experimenting_  to do.


End file.
